Toluene → 2'-Sulfamoyl-biphenyl-4-carboxylic acid

HRID 1392787Notes

Reaction equation

HRID 1392787 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:10])=[O:9].[C:12]([C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)([OH:14])=[O:13].C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(OCC)C>[NH2:11][S:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:18]1[CH:19]=[CH:20][C:15]([C:12]([OH:14])=[O:13])=[CH:16][CH:17]=1)(=[O:10])=[O:9]

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 3121834-Carboxyphenylboronic AcidHCID 28012632-Bromobenzenesulfonamide

Product 1

HCID 27605552'-Sulfamoyl-biphenyl-4-carboxylic acidYield 57.4%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

2-Bromobenzenesulfonamide (800 mg) and 4-carboxyphenylboronic acid (563 mg) were suspended in a mixed solvent of toluene (5 ml) and water (5 ml). Tetrakis(triphenylphosphine)palladium (392 mg) and anhydrous sodium carbonate (1.08 g) were successively added to the suspension, and the mixture was heated under reflux overnight. After the reaction mixture was cooled to room temperature, diethyl ether and water were added to conduct liquid separation. The resultant organic layer was extracted twice with water. The resultant water layers were all combined, and 12N hydrochloric acid was added to this solution to acidify it. The solution was concentrated to about 20 ml under reduced pressure. Colorless powder deposited was collected by filtration and dried under reduced pressure to obtain the title compound (539 mg).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. customliquid separation
  4. extractionThe resultant organic layer was extracted twice with water
  5. addition12N hydrochloric acid was added to this solution
  6. concentrationThe solution was concentrated to about 20 ml under reduced pressure
  7. filtrationColorless powder deposited was collected by filtration
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-bc99965c81c849a19ec6aa2d5ce765e5
Source dataset
uspto-grants-2008_03
Patent number
US07342014B2

Reaction notes

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